3-nitrophenethyl tert-butyl ether | 119273-88-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-nitrophenethyl tert-butyl ether
• 英文别名: 1-[2-[(2-Methylpropan-2-yl)oxy]ethyl]-3-nitrobenzene
• CAS: 119273-88-0
• 化学式: C₁₂H₁₇NO₃
• 分子量: 223.272
• InChiKey: KWNYIBGXQIUESI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-硝基苯乙烯 、 叔丁醇 以 formamide 为溶剂， 反应 1.0h， 生成 3-nitrophenethyl tert-butyl ether
  参考文献：
  名称：

  Photoaddition of water and alcohols to 3-nitrostyrenes. Structure-reactivity and solvent effects

  摘要：

  DOI：

  10.1021/jo00267a023

文献信息

• Ozone-Mediated Nitration of Phenylalkyl Ethers, Phenylacetic Esters, and Related Compounds with Nitrogen Dioxide. The Highest <i>Ortho</i> Substitution Observed in the Electrophilic Nitration of Arenes
  作者：Hitomi Suzuki、Toyomi Takeuchi、Tadashi Mori

  DOI：10.1021/jo9606867

  日期：1996.1.1

  Ey the combined action of ozonized oxygen and nitrogen dioxide (the kyodai-nitration), the title compounds were smoothly nitrated in dichloromethane at subzero degrees with high ortho positional selectivity. Although the conventional nitration of phenylacetic acid and esters mainly produces m- and p-nitro derivatives, the present nitration offers a simple high-yield synthesis of o-nitro derivatives which are important as precursor in organic synthesis, The proportions of the ortho isomer in the nitration products from methyl 2-phenylethyl ether and methyl phenylacetate were 71 and 88%, respectively, the latter value being the highest ortho isomer proportion so far observed in the electrophilic aromatic nitration. The observed high ortho selectivity has been rationalized in terms of radical cation intermediate and six-membered cyclic transition state.
• WAN, PETER;DAVIS, MICHAEL J.;TEO, MARY-ANNE, J. ORG. CHEM., 54,(1989) N, C. 1354-1359
  作者：WAN, PETER、DAVIS, MICHAEL J.、TEO, MARY-ANNE

  DOI：——

  日期：——